1. Field of the Invention:
This invention relates to a method for producing N-(2-chloroethyl) methanesulfonamide of high quality from ethylene imine and methanesulfonyl chloride with high productivity.
2. Description of the Prior Art:
N-(2-chloroethyl) methanesulfonamide is an important substance used mainly as an intermediate for photographic chemicals and is demanded to possess high quality.
The method for producing N-(2-chloroethyl) methanesulfonamide by the reaction of ethylene imine with methanesulfonyl chloride in the presence of an alcohol of 3 to 5 carbon atoms and/or a ketone of 3 to 10 carbon atoms is disclosed in JP-A-48-85,535.
In accordance with the method which produces N-(2-chloroethyl) methanesulfonamide by the reaction of ethylene imine with methanesulfonyl chloride in the presence of an alcohol of 3 to 8 carbon atoms and/or a ketone of 3 to 10 carbon atoms as disclosed in JP-A-48-85,535, however, since the reaction temperature must be controlled to a low temperature in the range of from 5.degree. C. to 10.degree. C. with a view to ensuring a high yield of reaction and preventing the product, N-(2-chloroethyl) methanesulfonamide, from coloration, the reaction velocity is low and the productivity is low.
If the reaction is carried out at a temperature exceeding 10.degree. C. for the purpose of improving the productivity of the method, the yield of the reaction is degraded because the reaction performed in the presence of an alcohol entails a secondary reaction of methanesulfonyl chloride with the alcohol. By the same token, the purity of the produced N-(2-chloroethyl) methanesulfonamide is degraded because the reaction performed in the presence of a ketone suffers prominent coloration of the produced N-(2-chloroethyl) methanesulfonamide and entails occurrence of a peculiar by-product incapable of separation by distillation. The same problem arises when both an alcohol and a ketone are used together.
An object of this invention, therefore, is to provide a novel method for the production of N-(2-chloroethyl) methanesulfonamide.
Another object of this invention is to provide a method for the production of N-(2-chloroethyl) methanesulfonamide of high quality with high productivity by the reaction of ethylene imine with methanesulfonyl chloride at an elevated temperature.